An efficient heterogeneous gold(I)-catalyzed hydration of haloalkynes leading to α-halomethyl ketones

References

• (a) De Kimpe, N.; Verhe, R. 1999, The Chemistry of α-Haloketones, α-Haloaldehydes, and α-Haloimines; Wiley: New York, (b) Erian, A.; Sherif, S.; Gaber, H. Molecules 2003, 3, 793–865. (c) Hintermann, L.; Labonne, A. Synthesis 2007, 1121–1150.
   Google Scholar
• (a) Gribble, G. W. Acc. Chem. Res. 1998, 31, 141–152. (b) Gribble, G. W. Chem. Soc. Rev. 1999, 28, 335–346. (c) Gribble, G. W. Heterocycles 2012, 84, 157–207. (d) Moragas, T.; Correa, A.; Martin, R. Chem. Eur. J. 2014, 20, 8242–8258. DOI: 10.1021/ar9701777
   Web of Science ®Google Scholar
• (a) Arabaci, G.; Guo, X.-C.; Beebe, K. D.; Coggeshall, K. M.; Pei, D. J. Am. Chem. Soc 1999, 121, 5085–5086. (b) Conde, S.; Perez, D. I.; Martinez, A.; Perez, C.; Moreno, F. J. J. Med. Chem. 2003, 46, 4631–4633. (c) Ostrowski, T.; Golankiewicz, B.; De Clercq, E.; Andrei, G.; Snoeck, R. Eur. J. Med. Chem. 2009, 44, 3313–3317. DOI: 10.1021/ja9906756
   Web of Science ®Google Scholar
• (a) Morton, H. E.; Leanna, M. R. Tetrahedron Lett. 1993, 34, 4481–4484. (b) VanBrunt, M. P.; Ambenge, R. O.; Weinreb, S. M. J. Org. Chem. 2003, 68, 3323–3326. (c) Patil, R. D.; Joshi, G.; Adimurthy, S.; Ranu, B. C. Tetrahedron Lett. 2009, 50, 2529–2532. (d) Nobuta, T.; Hirashima, S.-I.; Tada, N.; Miura, T.; Itoh, A. Synlett 2010, 2335–2339. (e) Gonzalez-de-Castro, A.; Xiao, J. J. Am. Chem. Soc. 2015, 137, 8206–8218. (f) Rajbongshi, K. K.; Hazarika, D.; Phukan, P. Tetrahedron Lett. 2015, 56, 356–358. DOI: 10.1016/0040-4039(93)88064-P
   Web of Science ®Google Scholar
• (a) Olah, G. A.; Ohannesian, L.; Arvanaghi, M.; Prakash, G. K. S.; J. Org. Chem. 1984, 4. 2032–2034. (b) Dickschat, J. S.; Reiichenback, H.; Wagner-Dobler, I.; Schulz, S. Eur. J. Org. Chem. 2005, 4141–4153. DOI: 10.1021/jo00185a046
   Google Scholar
• De Kimpe, N.; Brunet, P. Synthesis 1990, 1990, 595–596. DOI: 10.1055/s-1990-26953
   Google Scholar
• (a) Barluenga, J.; Martinez-Gallo, J. M.; Najera, C.; Yus, M. Synthesis 1986, 678–680. (b) Bekaert, A.; Barberan, O.; Gervais, M.; Brion, J.-D. Tetrahedron Lett. 2000, 41, 2903–2905.
   Google Scholar
• (a) Kosower, E. M.; Wu, G. S. J. Org. Chem. 1963, 28, 633–638. (b) Dieter, R. K.; Nice, L. E.; Velu, S. E. Tetrahedron Lett. 1996, 37, 2377–2380. (c) Kajigaeshi, S.; Kakinami, T.; Moriwaki, M.; Fujisaki, S.; Maeno, K. Okamoto, T. Synthesis. 1988, 545–546. DOI: 10.1021/jo01038a008
   Google Scholar
• (a) Tanemura, K.; Suzuki, T.; Nishida, Y.; Satsumabayashi, K.; Horaguchi, T. Chem. Commun. 2004, 470–471. (b) Meshram, H. M.; Reddy, P. N.; Vishnu, P.; Sadashiv, K.; Yadav, J. S. Tetrahedron Lett. 2006, 47, 991–995. (c) Pravst, I.; Zupan, M.; Stavber, S. Tetrahedron 2008, 64, 5191–5199.
   Google Scholar
• (a) Podgorsek, A.; Stavber, S.; Zupan, M.; Iskra, J. Green Chem. 2007, 9, 1212–1218. (b) Song, S.; Li, X.; Sun, X.; Yuan, Y.; Jiao, N. Green Chem. 2015, 17, 3285–3289. (c) Zheng, Z. B.; Li, Z. Z.; Han, B. B.; He, Z. M.; Shi, T. F.; Cheng, P. Tetrahedron Lett. 2015, 56, 2219–2222. (d) Rok, P.; Stojan, S. Tetrahedron Lett. 2014, 55, 5643–5647. (e) Rok, P.; Stojan, S. Adv. Synth. Catal. 2014, 356, 1266–1274. DOI: 10.1039/b707065a
   Web of Science ®Google Scholar
• (a) Xie, L.; Wu, Y.; Yi, W.; Zhu, L.; Xiang, J.; He, W. J. Org. Chem. 2013, 78, 9190–9195. (b) Ghosh, N.; Nayak, S.; Prabagar, B.; Sahoo, A. K. J. Org. Chem. 2014, 79, 2453–2462. (c) Starkov, P.; Rota, F.; D'Oyley, J. M.; Sheppard, T. D. Adv. Synth. Catal 2012, 354, 3217–3224. DOI: 10.1021/jo401437w
   PubMed Web of Science ®Google Scholar
• Chen, Z.-W.; Ye, D.-N.; Ye, M.; Zhou, Z.-G.; Li, S.-H.; Liu, L.-X. Tetrahedron Lett. 2014, 55, 1373–1375. DOI: 10.1016/j.tetlet.2014.01.027
   Web of Science ®Google Scholar
• Zou, H.; He, W.; Dong, Q.; Wang, R.; Yi, N.; Jiang, J.; Pen, D.; He, W. Eur. J. Org. Chem. 2016, 2016, 116–121. DOI: 10.1002/ejoc.201501198
   Google Scholar
• Park, J.; Yeon, J.; Lee, P. H.; Lee, K. Tetrahedron Lett. 2013, 54, 4414–4417. DOI: 10.1016/j.tetlet.2013.06.015
   Web of Science ®Google Scholar
• Zeng, M.; Huang, R.-X.; Li, W.-Y.; Liu, X.-W.; He, F.-L.; Zhang, Y.-Y.; Xiao, F. Tetrahedron 2016, 72, 3818–3822. DOI: 10.1016/j.tet.2016.04.049
   Web of Science ®Google Scholar
• Zou, H.; Jiang, J.; Yi, N.; Fu, W.; Deng, W.; Xiang, J. Chin. J. Chem. 2016, 34, 1251–1254. DOI: 10.1002/cjoc.201600417
   Web of Science ®Google Scholar
• Phan, N. T. S.; Sluys, M. V. D.; Jones, C. W. Adv. Synth. Catal. 2006, 348, 609–679. DOI: 10.1002/adsc.200505473
   Web of Science ®Google Scholar
• Yang, W.; Zhang, R.; Yi, F.; Cai, M. J. Org. Chem. 2017, 82, 5204–5211. DOI: 10.1021/acs.joc.7b00386
   PubMed Web of Science ®Google Scholar
• Kresge, C. T.; Leonowicz, M. E.; Roth, W. J.; Vartuli, J. C.; Beck, J. S. Nature 1992, 359, 710–712. DOI: 10.1038/359710a0
   Web of Science ®Google Scholar
• Lindner, E.; Salesch, T.; Brugger, S.; Hoehn, F.; Wegner, P.; Mayer, H. A. J. Organomet. Chem. 2002, 641, 165–172. DOI: 10.1016/S0022-328X(01)01313-4
   Web of Science ®Google Scholar
• Li, M.; Li, Y.; Zhao, B.; Liang, F.; Jin, L.-Y. RSC Adv. 2014, 4, 30046–30049. DOI: 10.1039/C4RA04736B
   Web of Science ®Google Scholar